


Love Letters From Levi

by otomekaidii



Series: Love for Levi [18]
Category: Shall We Date?: Obey Me!
Genre: Angst, Angst and Hurt/Comfort, Angst with a Happy Ending, Awkward Levi is Awkward, Best Friends, Comfort, Communication, Consent, Developing Relationship, Dorks, Dorks in Love, Emotional Hurt/Comfort, F/M, First Kiss, First Time, Fluff, Friends to Lovers, Friendship, Friendship/Love, Gen, Gender-Neutral Pronouns, Gender-neutral Reader, Getting to Know Each Other, Hugs, Insecurity, Jealousy, Letters, Light Angst, Love Confessions, Love Letters, M/M, Other, Other Additional Tags to Be Added, Pre-Relationship, Reader-Insert, Romantic Fluff, Self Confidence Issues, Self-Esteem Issues, Social Anxiety, Tooth-Rotting Fluff
Language: English
Status: In-Progress
Published: 2021-02-16
Updated: 2021-03-05
Packaged: 2021-03-18 14:42:25
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 33
Words: 4,978
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29491491
Author URL: https://archiveofourown.org/users/otomekaidii/pseuds/otomekaidii
Summary: You and Levi decide to exchange letters as your friendship deepens and you continue to get to know each other.This is a collection of “handwritten” letters exchanged between you (MC) and Levi. Each chapter is a new letter.This will be an ongoing series, so please make sure to subscribe to keep up to date if you want to make sure you don’t miss one. ❤️
Relationships: Leviathan (Shall We Date?: Obey Me!) & Reader, Leviathan (Shall We Date?: Obey Me!)/Reader
Series: Love for Levi [18]
Series URL: https://archiveofourown.org/series/2020585
Comments: 39
Kudos: 77





	1. Chapter 1

**Author's Note:**

> I headcanon that Levi writes letters to MC since it’s easier to talk about things that way than speaking out loud, and it’s more personal than a text message. 
> 
> (I’m sure he’s one of those people that doodles little anime characters all over the pages and decorates his envelopes. He probably has an impressive collection of kawaii stickers and Ruri-chan stationary too!)
> 
> I got this idea at 4am, so I hope this isn’t one of those things that sounded better in my head. 🙃 There really isn’t a plan for this besides showcasing the relationship between Levi and MC. So I guess we will just see how it goes. 😬

Dear Levi,

Thanks for the letter! It was really fun getting to read it in class. Made me feel like a kid again hehe.

I haven’t written letters with someone like this before, so I hope I do a good job. I’m not sure what to talk about for a first letter. Nothing too exciting happened today while I was at RAD.

I’m looking forward to the anime marathon we have planned for this weekend! Can’t wait to learn all about the love of your life - Ruri-chan!

Talk to you soon,

MC


	2. Chapter 2

Dear MC,

I wasn’t sure how to address the letter. Writing “Dear” seems so formal and old fashioned but I couldn’t think of an alternative. 

I’m glad you’re looking forward to the marathon. It’s going to be really long - so be prepared! I can understand if you don’t want to spend that much time with me, but once we start you better be ready to commit! I won’t let you leave until we’re finished! LOL

See ya later,  
Levi

PS - please don’t freak out! I won’t actually lock you in my room. 


	3. Chapter 3

Dear Levi,

Right now you’re busy with a video game, so I decided to write a letter to you while I wait. 

I just want you to know that I’m having a lot of fun with you. The anime was amazing, but getting to watch it with you and talk about it was what made it really special. I always love chatting with you and listening to your take on things. You’re really cute when you geek out like that, you know?

Anyways, thank you for having me over. I really enjoyed myself and I hope we can do this again soon. Maybe next time I can pick out the anime?

Your BFF,  
Henry


	4. Chapter 4

Dear Henry,

LOL Writing that felt even weirder than just the “dear” part...but I also really liked it. I hope that’s not too strange? It just feels like it’s something special between the two of us.

I didn’t know you were so bored you had time to write a letter. :( I'm so sorry! I just got so wrapped up in my game I lost track of time and I think I even forgot you were there at one point. I know that makes me the worst kind of friend, but I promise I’ll make it up to you. If you want, that is. I can understand if you would rather not spend more time with me. :(

Levi


	5. Chapter 5

Dear Lord of Shadow,

Levi, you are the best friend I could ask for. Honestly. Don’t be so hard on yourself, please?

I didn’t mind at all waiting for you to play your game. I get it. Sometimes you get so focused on something you just have to do it or you won’t be able to concentrate on anything else. It’s ok - I’m the same way. :)

I could have read a manga or a book, but I didn’t. I decided that I would rather write to you instead. So be happy that I cared that much about you that I chose you over a manga! ;) 

Now, if you’re still feeling guilty, and it’ll make you feel better, I give you permission to “make it up to me.” 😬

Looking forward to what you have planned,  
Henry


	6. Chapter 6

Dear Henry, 

Ack! You’re way too nice to me. I don’t deserve your forgiveness! But I promise I won’t make you regret it! I’ll plan something extra special for you! Just you wait!!!

Remember that game I told you about awhile ago? The one where you get to design your own magical girl? They finally announced the release date for it! I’m so excited!!!! Do you think you would want to go to the midnight release? 

Only if you want to! And no this isn’t your special thing I’m going to plan. I’ll just have to do something else for you to say thanks if you agree to come with me!

Usually going to these events isn’t a problem because everyone else is an otaku too...but this game got really popular with a certain demographic of normies so I’d feel really awkward standing in line surrounded by all these people. And what would I do if they tried to talk to me?!?! At least if you were there I would have someone to talk to and that would hopefully discourage people from interacting with me. I hope. 

Let me know what you think!

Lord of Shadow


	7. Chapter 7

Dearest Lord of Shadow,

It is my pleasure to inform you that I, the ever faithful Henry, will be accepting your invitation to (1) midnight release party. 

Just let me know the date and the time we are supposed to leave so I can get prepared. I haven’t been to one of these before, but I’m assuming that you’ll want to leave several hours early to get a good place in line? 

I’m also looking forward to seeing what special surprises you’ll come up with to thank me. I’m game for anything so long as I get to spend time with you!

Awaiting your reply,  
Henry


	8. Chapter 8

Dear Henry,

YAY!!!! I’m so happy that you’ll be coming with me! This is going to be amazing.

I was doing more research into the event locations, and I found one video game store that is going all out. They are even having a costume contest! You’ll cosplay with me, right?! I already have the perfect idea for what you can wear. We could match too, if you don’t think that’s too weird and gross? 

Tomorrow I don’t have anything to do, so I thought we could do one of your special things?

(I’m not saying that because I’m bored! I just mean I’m not busy?? I feel like that might be worse??? I’m just going to stop talking about that now.)

Meet me by the front door at 11 in the morning, on the dot! Dress comfortably for lots of walking! And I’ll take care of the rest.

Can’t wait to see you,  
Lord of Shadow


	9. Chapter 9

Dear Levi,

Today was amazing!!! The picnic you had planned was absolutely perfect. I know I oohh-ed and aww-ed plenty while we were out, but I seriously couldn’t get enough of the cute little bentos you made for us. It was like a shojo manga dream date!

I did want to check with you to make sure you were feeling ok though? You were a little jumpy on the way home and I wasn’t sure if I upset you or something? Or if you had just been outside for too long and were getting anxious?

Whatever it is, please let me know. I’m always here to listen if you want to talk. You’re my best friend and I want to take care of you!

Hope to hear from you soon,  
MC


	10. Chapter 10

Dear MC,

I’m glad that at least you enjoyed the picnic.

It was a colossal failure to me though. I had planned everything out to the last detail, but then nothing worked out! I still got anxious and nervous and I panicked! I was hoping you hadn’t noticed, but I guess you did, and I can’t decide if it’s worse knowing you were aware or if you hadn’t noticed? 

The truth is….I had something I wanted to tell you. Something really important. Like more important than the midnight release party. 

But I’m too much of a coward to tell you. I’m scared you’ll laugh (even though I know you wouldn’t), or worse - I’m scared you’ll be grossed out by me and won’t want anything to do with me anymore. I know that probably sounds dramatic to you since you don’t know what I’m talking about but it’s the truth. And a very real possibility. 

I think I just need some quiet time in my room to clear my thoughts.

Levi


	11. Chapter 11

Dear Levi, 

Why don’t you write me a letter about what it is you want to talk about?

I know you had plans and expectations for how the conversation and date would go, but it’s ok to change plans too you know? So if it’s easier for you to write things out, then take the time to write your thoughts down before you share them with me. 

I also want you to know that I’ll always be here for you. I don’t know what awful/important thing you have to discuss that has you so scared, but unless you’re going to admit to literally eating babies or something ridiculous like that, I know it won’t be a problem. You can tell me anything and I’ll always listen and be fair and honest with you, ok? 

And you’re definitely not a coward, Levi. You’re the furthest thing from one. 

Hope to hear more from you soon,   
MC


	12. Chapter 12

Dear MC, 

I really appreciate all the support and nice things you said in your last letter. You always just seem to know what to say to make me feel better. How do you do that?

I promise I’m not eating babies lol

The thing with the picnic is that I just wanted it to be perfect. It’s not like I get out a lot as it is, and I don’t often get a chance to show off something I’m actually confident in, you know? I really wanted to impress you and make you feel special too.

My plan had been to confess to you. You were right when you said it was like a shoujo manga dream date. That’s what I was going for. I remembered that one series you really liked and wanted to recreate that scene. But I chickened out. :( 

So I guess this is my confession? I know it’s not much. It’s not impressive and I’m still me. But I want to do better, I want to show you I can be better too. I’m not sure you’ll even want to be with me, but I know I want to be with you.

I love you. 

Love,  
Levi


	13. Chapter 13

Dear Levi, 

I love you too. 

Took you long enough. ❤️

Love,  
Your Henry


	14. Chapter 14

Dear Henry, 

Are you sure? Like really truly sure? You know who this is right?

This is Leviathan you’re talking to. 

You know, the yucky awkward shut in otaku that never leaves his room and lives off frozen pizza. That Levi. Are you sure you actually want to be confessing to him? Because he can’t figure out what you could possibly find so great about himself that you’d feel that way.

He’s also so ridiculously happy right now he’s writing about himself in the third person. I think you broke him. He might not be able to recover from this. 

But don’t worry, it’s a good kind of broken. ❤️

Love,  
Lord of Shadow

Ps. Don’t mind the damp spots on the paper. They are totally not from me crying. I just spilled some water.


	15. Chapter 15

My Levi, 

Oh sorry. I was trying to confess to my best friend Levi.

He’s this super talented otaku that knows how to design and make his own costumes. He’s even made video games before too. And he’s really good at karaoke and loves to draw when he has the time. Oh, and I can’t forget about all the AMV’s he’s made and remixed his own music for. 

Anyways, THATS the Levi I was trying to confess to.

So do you think you can pass on my message? 😉

Thanks!

Love,  
Your Henry


	16. Chapter 16

My Henry, 

Asmo caught me reading your letter in the library and is now convinced I was reading a dirty manga. I didn’t want to argue with him though because if he saw what I was actually reading I think it would be even more embarrassing.

Well, now I don’t know what else to say lol 

Maybe you could come by my room later and we could work on the costumes for the midnight release party? I need to make sure I have your measurements and everything right. 

Love,  
Your Levi

Ps. I love you


	17. Chapter 17

Dear Levi,

I had fun hanging out and working on the costumes with you last night. ❤️

But you really don’t need to be so embarrassed. First kisses are almost always awful. Teeth and spit everywhere, noses get in the way, people bump heads. That’s all normal. Just means we will have to practice more. :) 

You’re fine just the way you are. I hope you remember that.

Love,  
MC

PS. I love you too


	18. Chapter 18

Dear MC,

Thanks for always being so understanding. I wish I wasn’t so….awkward about everything. I don’t want to mess things up.

This is like a dream come true for me, you know? I never thought I’d be able to confess to someone, let alone find someone who’d be willing to accept it. It’s all kinda surreal. 

Part of me is even a little worried I’m going to wake up one morning and find out none of this actually happened, it was just a weird video game I got sucked into. Or even a dream.

I mean why would someone go for me when there are demons like Satan or Beel out there? Even Belphie is smarter than me, if you are into the whole tsundere thing. 

But I’m just me. And I don’t even know what I’m doing. My only experience with dating is in dating sims, but there aren’t any options here so I’m not sure what to say or do! What if I say the wrong thing and hurt you? Or what if I forget about something important? Are you sure you could be happy with someone like me?

Sorry for being such a downer. Guess that’s another thing that I have going against me. 

Love,  
Levi


	19. Chapter 19

My Levi,

I love you. 

I really really do. 

Please don’t overthink this, ok? You’re trying to get a million steps ahead of yourself right now. Just take a deep breath and stay with me, here, in the moment. 

Yes, there will probably be times that you hurt me. There will probably be times I hurt you too. That’s just how it works when you are getting closer to someone. And it’s ok. If something happens, we will talk about it, and work things out, and learn from it. 

And you don’t have to figure out all this stuff on your own either. You’ve got me with you now, right? Together I’m sure we can manage. No matter what the challenge is.

I’m also perfectly aware of just how awkward you are sometimes and how much of an otaku you are. And those are the very things I love about you the most. I hope, with time, you will come to understand that and realize just how much I care about you.

I just wish you could see yourself how I see you. ❤️

With more love than you can imagine,   
Your Henry


	20. Chapter 20

Dear Henry,

I’m not sure how you don’t get discouraged by my negativity all the time but...thanks. 

Thanks for sticking with me and talking to me when I get a little lost in my own head. It’s nice to know I have someone looking out for me like that. I guess that’s what you mean when you said relationships were about us working together, huh?

I plan on starting the costumes while you’re at RAD today. I think I’ll be able to get a lot done since I managed to work ahead in my classes last night. Can you stop by my room when you get back so I can have you try stuff on? I want to make sure I get it perfect for you because I know you’re going to look amazing.

Oh, and in case I didn’t mention it, the release party is in 2 weeks. We will probably leave around 8pm or so to get there early enough to participate in the costume contest. I think the author of the manga is supposed to be there too, so maybe we can get some signed copies while we’re at it? (Ok let me rephrase, we will be getting signed copies. Lol)

Thanks again for being patient with me. I can’t wait for you to get home.

Love,   
Lord of Shadow


	21. Chapter 21

My Lord, 

I know I already said this when I was with you earlier, but I want to say it again - the costume designs were really beautiful! I can tell how much effort you put into coming up with them and being accurate to both the manga and the game.

But...I’m not sure I’m comfortable wearing something like that. 

It’s not anything you did wrong! It just seems a little revealing to me? Which I guess I should have been prepared for since I am familiar with the manga series and I know what magical girls tend to wear in general. So that’s on me.

I’m just not sure if I can pull off the look. 

Please please please don’t be sad. Your costumes were absolutely lovely! I’m just feeling a little insecure I think.

Love,  
Your Henry 


	22. Chapter 22

My Henry,

I’m sorry I didn’t talk to you more about the designs when I sketched them earlier. :( I didn’t even think it might be a problem. I’d never want to do anything to make you uncomfortable!

I understand though being scared to go out all dressed up. I only created things for myself for the longest time because it’s honestly pretty scary going to cons by yourself in full cosplay. There are so many talented people there with way better costumes, it’s hard not to feel inadequate next to them. Plus people are always approaching you to try to take pictures! It’s so awkward. 

But after spending more time with you, it seems less scary now than it used to.

This will be the first time I’ve gone out in my own costume, btw. And I can only do it because I know you’ll be with me.

I guess what I’m trying to say is that I know what it’s like to feel insecure like that and wonder if you’re good enough. But we will be together this time and can look out for each other! 

Love,  
Lord of Shadow

ps. I’ve already started on a new design for you so don’t worry!


	23. Chapter 23

My Lord,

Thank you for being so sweet and understanding. ❤️

I’m sorry for being so much trouble, but thank you. You’re the best boyfriend I could have. ❤️ I can’t wait to see what you come up with. I’m sure it’ll be even more amazing than the first one too.

I love you!

Love,  
Your Henry

Ps. I love you! (Because I don’t think I can say it enough!)


	24. Chapter 24

Dear Henry,

I hope you had a good day at RAD today. It never used to bother me that everyone else went to in person classes while I did online ones...but now I’m getting more and more jealous that they get to spend more time with you during the day. Even though I know even if I went to RAD we probably wouldn’t even be in the same classes and I’d be stuck with a bunch of obnoxious normies. 

*sigh*

Anyways, I finished the sketches for costumes today so I hope you can look at them soon and give me your feedback. ☺️

Love,  
Lord of Shadow


	25. Chapter 25

Dear Levi,

I’d love it if you went to in person classes with me! I know that wouldn’t be easy for you, but maybe if we talk to Lucifer he can make some changes to my schedule so we could have more classes together? He’s always trying to encourage you to get out more, so I don’t see why he’d say no to accommodating you so that you could be at RAD too. 

Either way, it’s up to you. ❤️ I’ll try to text you more during the day if you decide to stay home too. 🙂

The sketches you showed me looked great! I know I said it already, but I really like the fuller skirt and the more opaque leggings. What I loved the most though was how you made it match yours. 🥺 you didn’t have to do that since I know you liked your original design so much, but it made me feel a lot better knowing they would still look like an obvious matching set. 

I’ll have to find some way to thank you this weekend. ☺️

Love,  
Your Henry


	26. Chapter 26

Dear Henry,

Ummmm what do you mean by “thank me”? 

Because like...you really don’t need to do anything. I’m not sure I’m ready for anything anyways. I just wanted to make you a nice costume, I don’t need thanks. Not that I don’t want thanks...it’s just...well. I’m still me. And I’m awkward.

And I think I’m going to cut this letter short because this is just getting weird.

Love,  
Levi


	27. Chapter 27

Dear Levi,

I’m so sorry for not saying something to you sooner. I wanted to talk to you right away but we had to leave for classes and you ran off before I could.

I just meant like baking you a cake or taking you somewhere, like a date.

I wasn’t talking about anything else.

So don’t worry about it, ok? I’m not in any rush and I would never pressure you into something like that. I just want to spend as much time with you as I can. 

This weekend we can just relax in your tub and watch one of your favorite anime. No strings attached or hidden motivations on my part. I promise. And I’m sorry for making you uncomfortable by thinking I was suggesting that before we talked about it. We can talk about it whenever you’re ready.

Love you bunches,  
Your Henry


	28. Chapter 28

Dear Henry,

Oh.

I guess come cupcakes would be ok. 

Do you think I could help? Or would that be weird since you’re supposed to be “thanking me”? I just like decorating and I could make them Ruri-chan themed and I thought it might be fun to do together. 

Sorry I’m such an awkward mess. Now I feel weird like I made you uncomfortable. I hope I didn’t. I don’t want to mess things up. 🙁

I just really like spending time with you too. A good hug is about all my heart can take right now. I’d probably faint if I did anything else and that would just be super embarrassing. And I embarrass myself enough as it is doing normal things, I don’t really want to go and do something that I know won’t end well for me. 

The new costumes should be ready for you to try on this weekend too, if you want. There’s still some details and things I have to do, but I want to make sure the sizing and fit is right first. 

Love,  
Your Lord of Shadow


	29. Chapter 29

My Lord of Shadow,

I love you, did you know that?

You didn’t make me feel uncomfortable at all, I promise. ❤️ And FWIW, I don’t think you’d have to worry too much about embarrassing yourself. You’d be with me, and no matter what happens, I’d still be on your side. I want you to feel safe with me. ❤️

But I’m more than happy to shower you in hugs and kisses too. ☺️ I just want you to feel loved and appreciated. So I hope you’re prepared for that tonight when I come hang out!

Love,  
Your Henry 

Ps. I can’t wait to see the costumes!


	30. Chapter 30

My Henry,

I don’t know how I managed to get so lucky to have you in my life. 

It feels weird to thank you for hugging me...but, thanks. I really enjoyed our time together this weekend. Maybe next time you could um, spend the night? If you’re comfortable with that I mean. Going back to your room at 1am seems like such a pain when you could just as easily stay in mine. 

I just really like having you around, and it feels weird when you have to leave even though I know you’re literally right down the hall. Almost enough to get me to leave my room. Almost. :P 

I’m glad you liked the costumes too! I’ll be finishing all the details up this week and I can’t wait until next weekend! We are going to win this cosplay contest for sure. Everyone will be so jealous of us! Having other people jealous of me will be nice for a change lol

Can’t wait to see you again and give you another hug,  
Your Lord of Shadow


	31. Chapter 31

My Lord of Shadow,

I’d love to stay the night sometime if that’s ok. ☺️ I know I’ve stayed before when I’ve fallen asleep during a movie or something, but I think it would be nice to just plan on staying and spending the whole night with you too. ❤️ 

And you know, you can always come visit me in my room lol It is just down the hall like you said. Mammon does tend to camp out in there though. 😂 

He was complaining the other day that I don’t spend enough time with him and I was wondering if maybe we could include him in a game night or movie night from time to time so he doesn’t feel left out? I know that might seem like a weird request, but he is still my friend and he is your brother and we hung out a lot together before.

So ready and excited for this weekend!!

Love,  
Your Henry


	32. Chapter 32

Dear Henry,

This letter is really hard for me to write. I’ve thrown it away and started over more times than I can count. I eventually practiced on plain white lined paper so I didn’t waste anymore of my good stationary…

First, I guess I owe you an apology for being a bit of an ass the past two days. Ok, a lot of an ass. I shouldn’t have ignored you or snapped at you when you tried to talk to me. We’re supposed to be partners, and I shut down and pushed you away, and I’m sorry. 

But reading about your friendship with Mammon was hard. 

I know that’s ridiculous because you’ve always been friends with him. And like you said, we frequently hang out together anyways. But since we confessed to each other I guess I kinda got it into my head that you were “mine” and since I didn’t see you much outside of when we were alone together, I sorta let myself forget that you’re close to my brothers too? 

I think part of it is he is such a wreck and yet you still care for him. But I feel like I have to try so hard to do the right thing and to impress you. And it’s just not fair that it seems so easy for him.

I’m not sure what else to say here besides “I’m sorry” again. So, I’m sorry. 

Love,   
Levi


	33. Chapter 33

Dear Levi, 

I love you.

Thank you for taking the time to apologize and to explain how you’ve been feeling. I honestly wanted to run to your room right away and talk to you face to face as soon as I read your letter, but I realized this would probably best be said in writing so that you can read it over and over again.

I love you so freaking much. I wish you could see yourself as I see you. You are so amazing and talented, and you’re constantly surprising me. 

You don’t have to try so hard to impress me, Levi. My favorite moments with you are when you open up and are just completely yourself. I love listening to you as you carry on about whatever show or game you’re currently obsessed with. It’s just so endearing to me. You are so happy in those moments, and I love seeing that. It doesn’t matter if I have no idea what you’re talking about or have zero interest in whatever it is. I just want to listen to you talk about something you love and watch how your eyes sparkle when you do. 

As for Mammon, I really think you should talk to him sometime. It might seem like he’s just being reckless and impulsive all the time...but he’s got his own share of anxieties that are similar to yours. And he wears himself out trying to impress me (and everyone else) too. Why do you think he’s taken to hiding in my room? It’s because it’s a safe and quiet place, and he knows that if he’s there with me, Lucifer and the others are far less likely to start shit with him.

But I want to make sure you understand something - He will never replace you. Ever. You’re both two different people (demons) and have two different roles to play in my life. I don’t compare the two of you either. And it doesn’t matter what he does or doesn’t do - you’re still you and you’re still the one that I love. 

I’m sorry for upsetting you, I know I could have worded my request better, but I still meant what I said. I’d like to hang out with Mammon more, because he is still my friend. That doesn’t mean I love you less or don’t want to spend time with you. It’s about finding a balance, and I think including him in some group activities would be good for that (not all the time, just sometimes). It’s kinda like how you have your Raid Nights with your guild. I’d never ask you to give those up or expect you to spend all your time with me, focused solely on me. 

Just please don’t forget how much I love you and how much you mean to me.

Love,  
Your Henry

**Notes for the Chapter:**

> I thought about making this into poly!MC but decided to stick with my original plan to just focus on Levi. 
> 
> I still love Mammon though so I hope he forgives me. 😭


End file.
